CHEBI:48947 - clavulanic acid

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ChEBI Name clavulanic acid
ChEBI ID CHEBI:48947
Definition Antibiotic isolated from Streptomyces clavuligerus. It acts as a suicide inhibitor of bacterial β-lactamase enzymes.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:43442, CHEBI:3736
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Formula C8H9NO5
Net Charge 0
Average Mass 199.16080
Monoisotopic Mass 199.048
InChI InChI=1S/C8H9NO5/c10-2-1-4-7(8(12)13)9-5(11)3-6(9)14-4/h1,6-7,10H,2-3H2,(H,12,13)/b4-1-/t6-,7-/m1/s1
InChIKey HZZVJAQRINQKSD-PBFISZAISA-N
SMILES [H][C@@]12CC(=O)N1[C@@H](C(O)=O)\C(O2)=C\CO
Metabolite of Species Details
Streptomyces clavuligerus (NCBI:txid1901) See: PubMed
Roles Classification
Biological Role(s): antibacterial drug
A drug used to treat or prevent bacterial infections.
bacterial metabolite
Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
EC 3.5.2.6 (beta-lactamase) inhibitor
An EC 3.5.2.* (non-peptide cyclic amide C-N hydrolase) inhibitor that interferes with the action of beta-lactamase (EC 3.5.2.6).
Application(s): antibacterial drug
A drug used to treat or prevent bacterial infections.
anxiolytic drug
Anxiolytic drugs are agents that alleviate anxiety, tension, and anxiety disorders, promote sedation, and have a calming effect without affecting clarity of consciousness or neurologic conditions.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing clavulanic acid (CHEBI:48947) has role antibacterial drug (CHEBI:36047)
clavulanic acid (CHEBI:48947) has role anxiolytic drug (CHEBI:35474)
clavulanic acid (CHEBI:48947) has role bacterial metabolite (CHEBI:76969)
clavulanic acid (CHEBI:48947) has role EC 3.5.2.6 (β-lactamase) inhibitor (CHEBI:35625)
clavulanic acid (CHEBI:48947) is a oxapenam (CHEBI:64509)
clavulanic acid (CHEBI:48947) is conjugate acid of clavulanate (CHEBI:487869)
Incoming clavulanate (CHEBI:487869) is conjugate base of clavulanic acid (CHEBI:48947)
IUPAC Name
(2R,3Z,5R)-3-(2-hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
INNs Sources
acide clavulanique ChemIDplus
ácido clavulánico ChemIDplus
acidum clavulanicum ChemIDplus
clavulanic acid ChemIDplus
Synonyms Sources
(2R,3Z,5R)-3-(2-HYDROXYETHYLIDENE)-7-OXO-4-OXA-1-AZABICYCLO[3.2.0]HEPTANE-2-CARBOXYLIC ACID PDBeChem
(Z)-(2R,5R)-3-(2-Hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo(3.2.0)heptane-2-carboxylic acid ChemIDplus
antibiotic MM 14151 ChemIDplus
Clavulanate KEGG COMPOUND
Clavulanic acid KEGG COMPOUND
Clavulansäure ChemIDplus
clavulonic acid
Note: (2015-04-15) A rare variant spelling.
ChEBI
MM 14151 ChemIDplus
Manual Xrefs Databases
1930 VSDB
669 DrugCentral
C00018091 KNApSAcK
C06662 KEGG COMPOUND
Clavulanic_Acid Wikipedia
D07711 KEGG DRUG
DB00766 DrugBank
DE2517316 Patent
HMDB0014904 HMDB
J01 PDBeChem
View more database links
Registry Numbers Types Sources
58001-44-8 CAS Registry Number KEGG COMPOUND
58001-44-8 CAS Registry Number ChemIDplus
58001-44-8 CAS Registry Number DrugBank
787059 Beilstein Registry Number Beilstein
787059 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
11092620 PubMed citation Europe PMC
12413541 PubMed citation Europe PMC
18450406 PubMed citation Europe PMC
19394358 PubMed citation Europe PMC
25047044 PubMed citation Europe PMC
25477926 PubMed citation Europe PMC
25763134 PubMed citation Europe PMC
25844706 PubMed citation Europe PMC
25998949 PubMed citation Europe PMC
27731424 PubMed citation Europe PMC
9131470 PubMed citation Europe PMC
Last Modified
22 February 2017